Oscars Fashion: Iconic Red Carpet Dresses and ’90s Style

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Photo by Ron Galella/Ron Galella Collection via Getty Images, Barry King/Liaison, Jim Smeal/Ron Galella Collection via Getty Images

Love it or hate it, the Oscars are back to their regular lineup. This year, the ceremony will return to the Dolby Theater and its usual late February slot for the first time since the pandemic began. A celebration of all things film – visionary filmmaking, evocative screenplays and tour de force performances – the annual ceremony is the big night of the film industry. And in front of her famous red carpet, a great evening for fashion too.

Since their inception, the Oscars have been home to some of the most iconic style moments in history. Among the 33 dresses with dedicated Wikipedia entries, 21 originally graced the ceremony red carpet. Over the years, Oscar style has had a huge impact on the fashion industry and its trend cycles. And in no decade has this been seen more than in the 90s. In 1991, Cindy Crawford’s red Versace launched a thousand counterfeits. Gwyneth Paltrow’s Ralph Lauren thrilled; Lizzy Gardiner’s AmEx dress caused a stir. Some dresses changed the spirit of the times, and some continue to influence today. Ahead of Sunday’s ceremony — and, of course, its red carpet — a look back at the most iconic Oscars outfits from the ’90s.

Photo by Ron Galella/Ron Galella Collection via Getty Images

Cindy Crawford, 1991

In 1991, Cindy Crawford attended the Oscars as a plus-one — and outdid everyone officially invited. Accompanying her then-boyfriend Richard Gere, the model wore a plunging fire truck red dress designed by Versace. Not only did the dress fly the night, but it influenced fashion trends in the early 90s, inspiring a slew of imitations and knockoffs for fans of the look. Since its turn on the red carpet, the dress has made Oscar history, earning its own entry on Wikipedia and a perennial spot on the ceremony’s all-time lists. A testament to her reputation, the dress sold at auction for just over $12,500 in 1999.

Geena Davis posing on the Oscars red carpet in a 1992 white dress

Photo by Miranda Shen/Fotos International/Getty Images

Geena Davis, 1992

Geena Davis has always been one to shoot an Oscar look. And in 1992 – the year she was nominated for Thelma and Louise – she pulled a show-stopper. If you find this Ruth Meyers look a bit over the top (corset, ruffled train, tights and party gloves?), then you’ve come to the right place. Describing his design notes to Time magazinesaid Geena, “I want to marry the Moulin Rouge at the Bal Noir et Blanc, and I want Christo and Jean-Claude to design the wedding dress and the wedding cake.” The campy tailoring landed Geena on worst-dressed lists of the year, but, nonetheless, it ended up becoming one of the most memorable Oscar looks of the decade.

Lizzy Gardiner wearing a gold American Express Card dress on the 1995 Oscars red carpet

Photo by Barry King/Liaison

Lizzy Gardiner, 1995

In 1995, Australian costume designer Lizzy Gardiner showed up on the Oscars red carpet wearing one of her own designs: a column dress made from 254 expired American Express gold cards. The outrageous, Paco Rabanne-esque dress was originally designed for comedy The Adventures of Priscilla, Queen of the Desert and drew inspiration from Sydney’s drag culture. The dress did not make it to the final cut of the film (AmEx banned it), but Lizzy decided to remove it from her archives for the ceremony. While the look was skewered by critics (Time called it “tacky” and Cosmos nicknamed him one of the “worst Oscar dresses of all time”), Lizzy had the last laugh: wearing her gold AmEx dress, she took home the award for best costume for the rest of her Priscilla suit.

nicole kidman posing on the oscars red carpet in a john galliano dress for dior couture 1997

Photo by Ke.Mazur/WireImage

Nicole Kidman, 1997

We love when a plus-one overshadows her date — especially when it’s Nicole Kidman. In 1997, Nicole walked the Oscars red carpet in a dress that would change Oscar fashion forever. The dress in question was an elaborate and electrifying chartreuse dress, designed by John Galliano of Dior. Compared to the typically tame award show costume, the quirky look – with its fur trim and ornate embroidery – was a major fashion risk. But one who paid. Red carpet correspondents dubbed the look as one of the awards show’s “first real couture dresses.” Beyond the ceremony of the evening, the dress moved the needle from the style of the Oscars to the more experimental styles that we know and love today.

jada pinkett smith in a versace ensemble with will smith at the 1997 oscars

Photo by Jim Smeal/Ron Galella Collection via Getty Images

Jada Pinkett Smith, 1997

Long before the many coats of maillooks of the year 2000, Jada Pinkett Smith wore Versace to the 1997 Oscars. The midriff-bearing metallic mesh ensemble was a bold departure from the typical awards show prom dresses, but captured the fashion zeitgeist perfectly – in 1997, Versace was the designer of the day. Without a doubt, this sexy and form-fitting look influenced the styles of future starsY2K to 2020.

Gwyneth Paltrow holding her oscar in a pink dress 1999

Photo by Jim Smeal/Ron Galella Collection via Getty Images

Gwyneth Paltrow, 1999

At the 1999 Oscars, Gwyneth Paltrow made headlines not only for her Best Actress award, but also for her dress: a Ralph Lauren ball gown in pink taffeta,As Gwyneth said vogue, the dress was custom-made just for her after she requested a similar pink skirt in the designer’s seasonal lookbook. (“That was the designer days,” she smiles.) At the time, the dress polarized fashion critics and fans alike. Some praised her return to Old Hollywood glam. Others derided its bubblegum hue. In the 21st century, however, the dress has still ranked among the most iconic Oscar dresses. It also has its own Wikipedia page.

Celine Dion posing in a backless tuxedo on the 1999 Oscars red carpet

Photo by Jim Smeal/Ron Galella Collection via Getty Images

Celine Dion, 1999

It’s the look that transformed Celine Dion from musical legend to fashion icon that she is today. In 1999, the singer walked the Oscars red carpet in a backwards Dior tuxedo (and fedora). At a time when women’s red carpet wear was limited to evening gowns, Dion’s look was criticized by fashion critics, who considered it too avant-garde. Of the risky set, Celine said People, “I was the only one who had pants in a backwards suit from Galliano and if I did that today, it would work.” Celine was just ahead of her time.

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